Jonathan Tolins and Mark Waldrop Share the Secrets of Creating the Drama Desk Awards

"Mark and I worked together once before," says Jonathan Tolins (Buyer & Cellar), writer of this year's Drama Desk Awards ceremony of the show's director, Mark Waldrop. "We both worked on Bette Midler's tour in 1999."

"Her Divine Miss Millennium tour," adds Waldrop.

For this year's event, the pair are drawing not only on their long-established working relationship, but also on their combined award-show experience that includes multiple past Drama Desk, Oscar, and Tony Award shows.

During a recent interview, Tolins and Waldrop pulled back the curtain on what it's like to create a theater-awards show and shared their thoughts on what makes the Drama Desks' New York theater's big night.

What do you see as the goal of awards shows?
Jonathan: Giving everyone something to shoot for, putting a punctuation mark on the end of a season and feeling good about the work that's been done. It's kind of like a party.

What are the unique challenges presented by awards shows in general?
Mark: I would say the biggest challenge is the amount of pre-planning and idiot-proofing you have to do. Behind the scenes, there's just this huge support system that has to be in place. The crew pulls a presenter out of the audience and gets them backstage into the correct wing before they're going to have to enter. They're handed everything they need back there. Someone talks it through with them, pats them on the back when it's time to walk onstage. Basically, I have to like put myself in the shoes of every person and just go, "Where am I confused? Where do I not know what to do?" And then you have to try to head that off.

Jonathan: I was interested to learn in the production meeting that there are actually only four physical awards that have to keep cycling through for presenters to give to recipients (they get their real awards in the mail later). So if you're on the wrong side of the stage, you're screwed. It's a lot of awards choreography.

But for me, writing an awards show is an exercise in humility because you have to realize that basically the material you're writing is not what's going to be memorable. What's going to be memorable is some acceptance speech or some surprise…So I try to keep it direct, fast, and funny. Where the show really is, is in the presentation of the awards and the performances from the shows.

What do you look for in collaborators for projects like this?
Jonathan: you look for the same things you look for in a friend. You look for someone smart, who has perspective, knows what's important and what isn't, and who has a good sense of humor.

What is the one thing you couldn't be without in producing a show like this?

Jonathan: Wi-fi. [laughs]

Mark: A master flowchart…There's just so many moving parts to keep track of. My big homework the last couple days was to turn in the chart with everyone's entrance and exit. That part is the least fun thing I ever get to do, but there is also a certain satisfaction to charting that out.

What advice would you give to someone trying to plan an awards show?
Jonathan: Have no ego because almost no presenter ever wants to say the first thing they're handed and you have to come up with alternates all the time. And that's fine, that's the job. Keep moving forward and trust that you're always going to come up with something that's smart and isn't going to embarrass anyone.

Walk me through what the day of is like for the two of you.
Mark: Well, I'll be there at 8 in the morning.

Jonathan: I'll be there at 11, handling incoming requests for changes to the script. But at that point I think most of the script will be on cards so it'll be less clerical work for me. I'll probably sit at a computer and type a new version of something and then I'll hand it off to whoever's going to put it on a card for the presenter.

Mark: They'll be moving in the sound equipment and the set and the lights and rolling in the podiums — all of that physical stuff. During the day we'll be having sound check for the performers and in some cases, it will be the first time I've heard what the performers will be doing. It's just last-minute crises or things that we have to fix, little fires to put out. But that's why preparation is important.

What is it about the Drama Desks Awards that attracted you to the job?
Jonathan: Because it's Broadway and off-Broadway and off-off-Broadway, I think the audience has a kind of camaraderie and communal feeling. It sort of is to the Tonys what the Golden Globes are to the Oscars — it's fun and a little looser. You feel like you're getting what people are really like.

Mark: And this show is the arena where the little off-Broadway show can go up against the big behemoth from Broadway.

Jonathan: Three years ago our host Michael Urie won solo performance for Buyer & Cellar opposite Bette Midler. [Tolins laughs] I don't know what ever happened to her.

The Drama Desk Awards airs live on TheaterMania.com on Sunday, June 4, at 8pm. Thankfully, this year Michael Urie takes on hosting duties and will not have to duke it out against Drama Desk nominee Bette Midler.